HCID 69883004, compound → HCID 23445615, compound

HRID 1871320Notes

Reaction equation

HRID 1871320 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:23]=[CH:22][CH:21]=[CH:20][C:8]=2[C:9]=1/[CH:10]=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH3:4]>CCOC(C)=O.[Pd]>[CH2:1]([C:5]1[O:6][C:7]2[CH:23]=[CH:22][CH:21]=[CH:20][C:8]=2[C:9]=1[CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 69883004HCID 69883004, compound

Product 1

HCID 23445615HCID 23445615, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

At ambient temperature, a solution containing cis-2-butyl-3-[2-(4-methoxy-phenyl)-vinyl]-benzofuran (0.400 g, 1.31 mmol) in EtOAc (5 mL) and 10% palladium on carbon (200 mg) was stirred under H2 (atmospheric conditions). The reaction was filtered and the filtrate concentrated to the title compound as a clear oil. 1H NMR (DMSO-d6) δ 0.83 (t, 3 H), 1.20 (sextet, 2 H), 1.37 (quintet, 2 H), 2.49-2.52 (m, 2 H, with DMSO), 2.78-2.85 (m, 4 H), 3.68 (s, 3 H), 6.78 (d, 2 H), 7.03 (d, 2 H), 7.17-7.21 (m, 2 H), 7.41-7.43 (m, 1 H), 7.54-7.56 (m, 1 H). IR (KBr) 2950, 1610, 1510, 1450 and 1250 cm-1. mass spectrum (EI) m/z 308 (M+). Anal. Calcd. for C21H24O2 : C, 81.78; H, 7.84; N, 0.00. Found: C, 81.55; H, 7.57; N, 0.10.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationthe filtrate concentrated to the title compound as a clear oil

Sources & evidence

ORD record
ord-6279f5147b4b437dac4ff2309a4ab4a3
Source dataset
uspto-grants-2000_08
Patent number
US06103708

Reaction notes

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